Methylamine → HCID 86641328, compound

Participants

Reaction Steps

Sodium triacetoxyborohydride (16 mg) was added to a mixture composed of di-tert-butyl {2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]-8-oxo-2,7,8,9-tetrahydro-6-thia-1,2,3,5-tetraazabenzo[cd]azulen-4-yl}imidodicarbonate of Example 40 (28 mg), dichloroethane (0.5 mL), a 2 N solution of methylamine in tetrahydrofuran (0.1 mL) and acetic acid (6 μL), and the mixture was stirred at room temperature for 17 hours. Methanol (three drops) was added dropwise to the reaction mixture, and then a 0.2 N sodium hydroxide solution was added, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and filtered, and then the filtrate was concentrated under reduced pressure. Dichloromethane (2 mL) and trifluoroacetic acid (0.5 mL) were added to the resulting residue, and the mixture was stirred at room temperature for two hours. The reaction mixture was concentrated under reduced pressure, and the resulting residue was purified by reversed phase liquid chromatography. A 4 N solution of hydrochloric acid in dioxane (20 μL) was added to the resulting solid. Methanol and diethyl ether were added and the precipitated solid was collected by filtration to obtain the title compound (5.7 g, 28%) as a solid.

Provenance & Evidence